Conventionally, an α-hydroxy ketone has been synthesized by first converting a ketone into an enolate or an equivalent thereof once, and then causing a diastereoselective reaction or an enantioselective reaction (see non-patent literature 1).
As an example of such a method, the method which converts a ketone into a lithium enolate, and causes optically active oxadilysine as an oxidizer to act thereon as an oxidizer (see patent literatures 2 to 8); the method which, as an asymmetric catalytic reaction, converts a ketone into an enol ether, and then carries out asymmetric dihydroxylation thereof (see non-patent literatures 9 to 10); and the technique which further carries out asymmetric epoxidation thereof (non-patent literatures 10 to 14), are known.
As described above, with these methods, it is necessary to first convert a ketone into the corresponding enolate or an equivalent thereof, and the catalytic asymmetric oxidation reaction has presented the problem that substrates with which a high asymmetric yield can be achieved are limited. Further, there has been another problem in that the asymmetric catalytic reaction requires use of an environmentally harmful metallic salt.
Recently, a method for synthesizing an α-aminooxy ketone by converting a ketone into a tin enolate, and then carrying out an asymmetric catalyzed reaction using nitrosobenzene using a catalytic amount of an optically active activating agent has been reported (non-patent literature 15).
The α-aminooxy ketone can be easily converted into an α-hydroxy ketone, thus this technique provides a part of a useful α-hydroxy ketone synthesizing method.
However, although this method requires a smaller amount of optically active catalyst, it has presented problems in that, for example, there is the need to first convert a ketone into a tin enolate; the tin compound has toxicity; and that the asymmetric catalyst used must be prepared from BINAP and AgOTf.
Thus, no excellent method for manufacturing an optically active α-hydroxy ketone directly from a ketone by an asymmetric catalytic reaction using an easily available asymmetric source as an activating agent has been provided. In addition, no manufacturing method which proceeds with high yield and asymmetric yield, meeting the requirements for practical use, has been available. In other words, no efficient manufacturing method from a ketone to an optically active α-hydroxy ketone has been provided.
Non-patent literature 1: Zhou et al. (Zhou, P.; Chen, B. C.; Davis, F. A. “Asymmetric Oxidation Reactions”, Katsuki, T., Ed.; Oxford University Press: Oxford, 2001; p 128)
Non-patent literature 2: Davis et al. (Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919)
Non-patent literature 3: Davis et al. (Davis, F. A.; Haque, M. S. J. Org. Chem. 1986, 51, 4083)
Non-patent literature 4: Chen et al. (Chen, B. C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, A. B. Tetrahedron 1991, 47, 173)
Non-patent literature 5: Davis et al. (Davis, F. A.; Kumar, A. J. Org. Chem. 1992, 57, 3337)
Non-patent literature 6: Davis et al. (Davis, F. A.; Weismiller, M. C.; Murphy, C. K.; Reddy, R. T.; Chen, B. C. J. Org. Chem. 1992, 57, 7274)
Non-patent literature 7: Davis et al. (Davis, F. A.; Kumar, A.; Reddy, R. T.; Rajarathnam, E.; Chen, B. C.; Wade, P. A.; Shah, S. W. J. Org. Chem. 1993, 58, 7591)
Non-patent literature 8: Davis et al. (Davis, F. A.; Clark, C.; Kumar, A.; Chen, B. C. J. Org. Chem. 1994, 59, 1184)
Non-patent literature 9: Hashiyama et al. (Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 8463)
Non-patent literature 10: Hashiyama et al. (Hashiyama, T.; Morikawa, K.; Sharpless, K. B. J. Org. Chem. 1992, 57, 5067)
Non-patent literature 11: Fukuda et al. (Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389)
Non-patent literature 12: Adam et al. (Adam, W.; Rainer, T. F.; Stegmann, V. R.; Saha-Moller, C. R. J. Am. Chem. Soc. 1998, 120, 708)
Non-patent literature 13: Zhu et al. (Zhu, Y.; Yu, Y.; Yu, H.; Shi, Y. Tetrahedron Lett. 1998, 39, 7819)
Non-patent literature 14: Adam et al. (Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C-G Tetrahedron: Asymmetry 1998, 9, 397)
Non-patent literature 15: Momiyama et al. (Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc., 2003, 125, 6038)